Synthesis of 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid derivatives via Ugi reactions

Ildikó Schuster, Anita Sztojkov-Ivanov, L. Lázár, F. Fülöp

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The three-component Ugi reactions of 3,4-dihydroisoquinolines, isocyanides and acids furnished 2-acyl-N-substituted-1,2,3,4-tetrahydroisoquinoline-1-carboxamides in moderate to good yields. Chiral, non-racemic acids induced only poor diastereoselectivities in the condensations. Hydrolysis of the Ugi carboxamides gave the corresponding 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acids, which due to their ready ability to undergo racemization, were obtained as racemic mixtures or with low enantiomeric excesses.

Original languageEnglish
Pages (from-to)102-108
Number of pages7
JournalLetters in Organic Chemistry
Volume4
Issue number2
DOIs
Publication statusPublished - Mar 2007

Fingerprint

Carboxylic Acids
Derivatives
Acids
Cyanides
Condensation
Hydrolysis
1,2,3,4-tetrahydroisoquinoline
1,2,3,4-tetrahydroisoquinoline carboxylic acid
G 1616

Keywords

  • α-amino acids
  • Isoquinolines
  • Ugi reaction

ASJC Scopus subject areas

  • Organic Chemistry
  • Biochemistry

Cite this

Synthesis of 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid derivatives via Ugi reactions. / Schuster, Ildikó; Sztojkov-Ivanov, Anita; Lázár, L.; Fülöp, F.

In: Letters in Organic Chemistry, Vol. 4, No. 2, 03.2007, p. 102-108.

Research output: Contribution to journalArticle

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